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Looking for high‐energy density compounds among hexaazaadamantane derivatives with CN, NC, and ONO 2 groups
Author(s) -
Xu Xiao Juan,
Xiao He Ming,
Ma Xiu Fang,
Ju Xue Hai
Publication year - 2006
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.20909
Subject(s) - isodesmic reaction , substituent , chemistry , detonation , density functional theory , standard enthalpy of formation , computational chemistry , detonation velocity , medicinal chemistry , organic chemistry , explosive material
Density functional theory (DFT) was employed to evaluate the heats of formation (HOFs) for hexaazaadamantane (HAA) derivatives with CN, NC, and ONO 2 groups, respectively. This was done by designing isodesmic reactions at the B3LYP/6‐31G* level of theory, where the HAA cage skeletons were kept unbroken to produce more accurate results, and all HOFs for the required reference compounds, NH 2 CN, NH 2 NC, NH 2 ONO 2 , and (CH 2 NH) 3 , were derived from the G 3 theory calculation based on the atomization energies. The calculation results show that the HOFs of HAA derivatives are mainly affected by the number and the position of substituent groups, all the obtained HOFs are positive, and the NC derivatives have the most HOFs among the three types of derivatives with the same number of substituent groups. The detonation velocity ( D ) and detonation pressure ( P ) were obtained from the empirical Kamlet–Jacobs equations. All the NC and CN derivatives of HAA have lower densities (ρ), heats of explosion ( Q ), D , and P . However, these properties of ONO 2 derivatives are rather high and vary with the number of ONO 2 groups. Considering the easiness for synthesis and relative stability, 2,4,6,8‐hexaazaadamantanenitrate is finally recommended as a potential candidate of a high‐energy density compound (HEDC). © 2006 Wiley Periodicals, Inc. Int J Quantum Chem, 2006